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Related Concept Videos

Frequency-dependent Selection01:21

Frequency-dependent Selection

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When the fitness of a trait is influenced by how common it is (i.e., its frequency) relative to different traits within a population, this is referred to as frequency-dependent selection. Frequency-dependent selection may occur between species or within a single species. This type of selection can either be positive—with more common phenotypes having higher fitness—or negative, with rarer phenotypes conferring increased fitness.
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Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

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In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
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Halogens03:01

Halogens

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Group 17 elements, known as halogens, are nonmetals. At room temperature, fluorine and chlorine are gases, bromine is a liquid, and iodine a solid. Astatine is a highly unstable radioactive element, so currently, most of its properties are unknown due to its short half-life. Tennessine is a synthetic element also predicted to be in this group. 
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Functional Groups02:45

Functional Groups

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Functional groups are a group of atoms with characteristic properties, which when linked to the carbon skeleton of a molecule, alter the properties of that molecule. For example, the presence of certain functional groups on a molecule will make them hydrophilic, whereas others will make them hydrophobic. These functional groups are an indispensable part of organic chemistry and important components of biological molecules, such as carbohydrates, proteins, lipids, and nucleic acids. Each...
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Structure of Alkanes02:23

Structure of Alkanes

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The formation of carbon-carbon bonds leading to the creation of the carbon chain is the basis of organic chemistry. August Kekulé and Archibald Scott Couper independently developed this idea of carbon chain formation.
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Nomenclature of Alkanes02:22

Nomenclature of Alkanes

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In the late 19th-century, the number of new chemical compounds discovered increased tremendously. Hence, the necessity arose to develop a naming system for the systematic nomenclature of these newly discovered compounds. IUPAC (International Union for Pure and Applied Chemistry), established in 1919, sets rules for the nomenclature.
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Surface Functionalization of Metal-Organic Frameworks for Improved Moisture Resistance
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Halogen-Dependent Surface Confinement Governs Selective Alkane Functionalization to Olefins.

Guido Zichittella1, Matthias Scharfe1, Begoña Puértolas1

  • 1Institute for Chemical and Bioengineering, Department of Chemistry and Applied Biosciences, ETH Zurich, Vladimir-Prelog-Weg 1, 8093, Zurich, Switzerland.

Angewandte Chemie (International Ed. in English)
|January 16, 2019
PubMed
Summary
This summary is machine-generated.

The choice of halogen dictates product distribution in alkane functionalization. Iron phosphate catalysts show superior olefin selectivity in oxychlorination due to surface reactions, unlike oxybromination

Keywords:
density functional theoryhydrogen halidesolefin selectivityoperando spectroscopiesreaction mechanisms

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Area of Science:

  • Catalysis
  • Surface Chemistry
  • Reaction Mechanisms

Background:

  • Direct alkane functionalization via oxyhalogenation is crucial for chemical synthesis.
  • Product distribution is highly sensitive to the specific halogen used.
  • Understanding reaction mechanisms is key to controlling selectivity.

Purpose of the Study:

  • To elucidate the distinct reaction mechanisms of oxychlorination and oxybromination of alkanes over an iron phosphate catalyst.
  • To explain the superior selectivity towards olefins in oxychlorination compared to oxybromination.
  • To correlate catalyst performance with detailed mechanistic insights.

Main Methods:

  • Operando surface-coverage analysis and gas-phase radical identification.
  • Kinetic studies combined with advanced characterization (prompt-gamma activation analysis, photoelectron photoion coincidence spectroscopy).
  • Density functional theory (DFT) calculations to rationalize experimental observations.

Main Results:

  • Oxychlorination proceeds via a surface-confined reaction, yielding high olefin selectivity.
  • Oxybromination involves a gas-phase radical-chain mechanism, leading to undesired byproducts.
  • Chlorine's molecular effects are pivotal in differentiating reaction pathways and selectivity.

Conclusions:

  • The reaction mechanism (surface-confined vs. gas-phase radical) dictates selectivity in alkane oxyhalogenation.
  • Iron phosphate catalysts exhibit halogen-dependent performance.
  • Detailed mechanistic studies are essential for designing selective catalytic processes.